CN106459831A - Improvements in or relating to organic compounds - Google Patents

Improvements in or relating to organic compounds Download PDF

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Publication number
CN106459831A
CN106459831A CN201580022826.0A CN201580022826A CN106459831A CN 106459831 A CN106459831 A CN 106459831A CN 201580022826 A CN201580022826 A CN 201580022826A CN 106459831 A CN106459831 A CN 106459831A
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salicylic acid
ester
alcohol
phenyl
methyl
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CN106459831B (en
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J-P·巴克曼
F·弗拉克斯曼
R·W·吉瑟
M·穆勒
C·凯莱
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Givaudan SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

A liquid fragrance composition consisting essentially of:- cyclohexylidene phenyl acetonitrile; and one or more ingredients selected from the group consisting of cyclohexyl salicylate, MEFROSOL<TM> (3-methyl-5-pheriyl-pentan-1-ol), HEDIONE<TM> (methyl 2-(3-oxo-2- pentylcyclopentyl)acetate), diethyl phthalate, isopropyl myristate, amyl salicylate, iso-amyl salicylate, benzyl salicylate, iso-bornyl salicylate, cis-3 hexenyl salicylate, ethyl salicylate, iso-butyl salicylate, methyl salicylate and phenylethyl salicylate; and optionally one or more of 3-methyl-5-phenylpentan-1-ol (MEFROSOL<TM>); an alcohol comprising more than 3 carbon atoms selected from the group consisting of benzyl alcohol, 1-hexanol, 1-heptanol, 1-octanol, cyclohexanol, cyclohexyl propanol, methyl phenyl carbinol, phenyl ethyl alcohol and dimethyl benzyl carbinol; or a glycol ether.

Description

In organic compound or associated improvement
The present invention relates to the stock solution containing cyclohexylidene phenylacetonitrile and the consumption containing described stock solution are produced Product.
Cyclohexylidene phenylacetonitrile (more commonly passes through title Paeonia suffruticosa nitrileTMKnown) be a kind of high value spice become Point, have and have been characterized as being Rose Essentielle, QINGXIANG, metal abnormal smells from the patient that is fragrant and making one to remember Herba Erodii.Paeonia suffruticosa nitrileTMNearly all It is all strength, relatively non-volatile and highly stable in medium.It has very high direct in wet method and dry method laundry Property, and it is favorably improved the strong of feature perfume and persistency.Therefore, it has been widely used in from fine perfumery to change The consumer products of the form of ownership of cosmetic, personal nursing and household care products.This molecule and its as fumet purposes retouch State in US6,069,125.
Although this molecule achieves huge business success, we have found that and it is mixed simultaneously with other fragrance components A not always simple thing.Especially, applicant have discovered that low temperature storage some under the conditions of cyclohexylidene phenyl Acetonitrile will crystallize.Especially, crystallization can occur at a temperature of below about 28 DEG C, particularly when liquid and irregular packaging When surface or solid impurity contact.Crystallization leads to quickly solidifying very much of bulk material, and formulator is wished this material Unique remedial measure that material is mixed with other compositions is that heating stores its container.Which increase process time and cost, and When carefully not carrying out heating stepses, may lead to produce and undesirable burn abnormal flavour.
The fusing point of specific objective material can be by reducing it with second material mixing, and this second material has I) lower fusing point, or ii) form eutectic mixture with described target substance.Although however, there may be many can drop The composition of the fusing point of low target material, but target substance and second material must need the whole temperature model of liquid condition It is thermodynamic compatibility (being that they should not be separated) in enclosing.In addition, under less than its liquid-solid phase separation temperature thermodynamically Compatible liquid mixture must keep such, even if impurity is not intended to or is intentionally added in liquid mixture, or if Liquid mixture is contacted with the surface that may produce nucleus site.
Another requirement in field of perfumery is, the mixture of target substance and second material is from the viewpoint of perfumery For must be acceptable in olfactory sensation, i.e. the mixture of material should have the abnormal smells from the patient being substantially similar to pure target substance Point to (direction) and odour intensity.
Find that suitable composition is combined with cyclohexylidene phenylacetonitrile to provide the fluid composition meeting above-mentioned requirements Thing is not direct.For example, those skilled in the art are it is expected that be very similar to cyclohexylidene phenylacetonitrile in structure Fragrance component PETALIATMThe eutectic mixture of thermodynamic compatibility can be produced, it will keep liquid to low temperature, and this Also will be very favorable, because cyclohexylidene phenylacetonitrile and PETALIATMSimilar olfactory sensation point to.However it has been found that this is not It is practical situation.Those skilled in the art are it is also foreseeable that the extensive fluid organic material matter such as liquid perfume material selecting and molten Agent can generate the binary mixture of thermodynamic compatibility within the scope of wide temperature with cyclohexylidene phenylacetonitrile.However it has been found that This is not practical situation.Especially, there are other fragrance components of the olfactory sensation sensing similar with cyclohexylidene phenylacetonitrile such as Phenylethyl alcohol, Phenoxyethyl alcohol, rose oxideTM, super Herba ConvallariaeTM(6- ethyl -3- methyl -6- octen-1-ol), dimethyl Benzyl carbinol, POMAROSETM(5,6,7- trimethyl -2,5- octadiene -4- ketone), new Flos Rosae Rugosae esterTM(2,2- neopentanoic acid benzene Base ethyl ester), PEOMOSATM(2- aminomethyl phenyl ethyl alcohol), ROSAPHENTM(2- methyl -5- phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyrrole MutterTM(2- methyl -4- methylene -6- phenyl-tetrahydro -2H- pyrans), diphenyl ether, remember promiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyl Base ethyl) -5- hexahydrotoluene), 3- methyl -2- phenyl but-2-ene nitrile, 3- ethyl -2- phenyl amyl- 2- alkene nitrile or (Z) -2- benzene Base hex- 2- alkene nitrile, nor form the liquid dihydric compositionss of thermodynamic compatibility with cyclohexylidene phenylacetonitrile.Further Ground, lower alcohol such as ethanol and isopropyl alcohol；And glycol ethers, such as propylene glycol, dipropylene glycol, DOWANOLTMPM or DOWANOLTMDPM is not the material being suitable to mix in compatible binary mixture with cyclohexylidene phenylacetonitrile.
Present application addresses the potential problems related to the process of cyclohexylidene phenylacetonitrile and storage, and in first party Face substantially overcomes them by the liquid fragrance composition of following material composition by providing：
Cyclohexylidene phenylacetonitrile；With
Component A, it is one or more of to be selected from the group composition：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl- 5- phenyl-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), O-phthalic Sour diethyl ester, isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid is different Norbornene ester, salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester, salicylic acid Phenylethylester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With optional
Component B, it is one or more of following material：Rose oxideTM, super Herba ConvallariaeTM(6- ethyl -3- methyl -6- Octen-1-ol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- trimethyl -2,5- octadiene -4- ketone), new Flos Rosae Rugosae esterTM (PA phenylethylester), PEOMOSATM(2- aminomethyl phenyl ethyl alcohol), ROSAPHENTM(2- methyl -5- benzene Base-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-tetrahydro -2H- pyrans), diphenyl ether, remember promiseTM(1- hydroxyl Base -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- phenyl but-2-ene nitrile, 3- ethyl -2- phenyl Amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise the alcohol more than 3 carbon atoms, selected from benzylalcohol, 1- hexanol, 1-heptanol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol and dimethyl benzyl carbinol；Glycol ethers.
In specific embodiments of the present invention, described liquid fragrance composition is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is one or more of to be selected from the group composition：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl- 5- phenyl-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), O-phthalic Sour diethyl ester, isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid is different Norbornene ester, salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester and salicylic acid Phenylethylester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester).
In other embodiments of the present invention, described liquid fragrance composition is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the salicylate in being selected from the group：Salicylic acid cyclohexyl ester, salicylic acid benzyl ester, the different ice of salicylic acid Piece ester and salicylic acid phenylethylester.
In other embodiments of the present invention, described liquid fragrance composition is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the composition in being selected from the group：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- phenyl-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), phthalic acid diethyl Ester, isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, Salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester, salicylic acid phenylethyl Ester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With
Component B, it is one or more of following material：3- methyl -5- phenyl amyl- 1- alcohol (Flos Rosae Rugosae alcoholTM), Flos Rosae Rugosae EtherTM, super Herba ConvallariaeTM(6- ethyl -3- methyl -6- octen-1-ol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- front three Base -2,5- octadiene -4- ketone), new Flos Rosae Rugosae esterTM(PA phenylethylester), PEOMOSATM(2- aminomethyl phenyl Ethyl alcohol), ROSAPHENTM(2- methyl -5- phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-four Hydrogen -2H- pyrans), diphenyl ether, remember promiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- Phenyl but-2-ene nitrile, 3- ethyl -2- phenyl amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise more than 3 carbon atoms Alcohol, selected from benzylalcohol, 1- hexanol, 1-heptanol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol and Dimethyl benzyl carbinol；Or glycol ethers.
In other embodiments of the present invention, described liquid fragrance composition is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the composition in being selected from the group：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- phenyl-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), phthalic acid diethyl Ester, isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, Salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester, salicylic acid phenylethyl Ester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With
Component B, it is amyl- 1- alcohol (the Flos Rosae Rugosae alcohol of 3- methyl -5- phenylTM), rose oxideTM, super Herba ConvallariaeTM(6- ethyl- 3- methyl -6- octen-1-ol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- trimethyl -2,5- octadiene -4- ketone), newly Flos Rosae Rugosae esterTM(PA phenylethylester), PEOMOSATM(2- aminomethyl phenyl ethyl alcohol), ROSAPHENTM(2- first Base -5- phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-tetrahydro -2H- pyrans), diphenyl ether, note PromiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- phenyl but-2-ene nitrile, 3- ethyl - 2- phenyl amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise the alcohol more than 3 carbon atoms, selected from benzylalcohol, 1- hexanol, 1- Enanthol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol and dimethyl benzyl carbinol；Or glycol Ether.
As used in this article, term " glycol ethers " includes selected from propylene glycol, dipropylene glycol, and 1- methoxyl group- 2- propanol DOWANOLTMPM or 2- (2- methoxy propoxy) propyl- 1- alcohol DOWANOLTMThe compound of DPM.
In one embodiment of the invention, liquid fragrance composition substantially by cyclohexylidene phenylacetonitrile and Salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid phenylethylester and optional 3- methyl- 5- phenyl amyl- 1- alcohol (Flos Rosae Rugosae alcoholTM) composition.
In one embodiment of the invention, liquid fragrance composition substantially by cyclohexylidene phenylacetonitrile and Salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid cyclohexyl ester or salicylic acid phenylethyl Ester；With optional benzyl alcohol or 1- hexanol, 1-heptanol or 1- capryl alcohol or Hexalin or methyl phenyl carbinol or phenylethyl alcohol or Dimethyl benzyl carbinol forms.
In one embodiment of the invention, liquid fragrance composition is substantially by cyclohexylidene phenylacetonitrile； With salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid phenylethylester；With optional glycol Ether forms, and more particularly still, wherein said glycol ethers are propylene glycol or dipropylene glycol or 1- methoxy-2-propanol DOWANOLTMPM or 2- (2- methoxy propoxy) propyl- 1- alcohol DOWANOLTMDPM.
In specific embodiments of the present invention, described liquid fragrance composition is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the salicylate in being selected from the group：Salicylic acid cyclohexyl ester, salicylic acid amyl group ester, salicylic acid isoamyl Base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid is different Butyl ester, salicylic acid ester, salicylic acid phenylethylester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With
One of following material：Flos Rosae Rugosae alcoholTM(3- methyl -5- phenyl-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), diethyl phthalate, isopropyl myristate, rose oxideTM, Or super Herba ConvallariaeTM(6- ethyl -3- methyl -6- octen-1-ol), or dimethyl benzyl carbinol, or POMAROSETM(5,6,7- tri- Methyl -2,5- octadiene -4- ketone), or new Flos Rosae Rugosae esterTM(PA phenylethylester), or PEOMOSATM(2- first Base phenylethyl alcohol), or ROSAPHENTM(2- methyl -5- phenyl-amyl- 1- alcohol), or Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene Base -6- phenyl-tetrahydro -2H- pyrans), or diphenyl ether, or note promiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- methyl Hexamethylene), or 3- methyl -2- phenyl but-2-ene nitrile, or 3- ethyl -2- phenyl amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene Nitrile.
When popular name used herein or trade name are to describe fragrance component, skilled fragrance manufacturers will be understood that this The title that Xie Shi perfumer is usually used.However, those skilled in the art are it will also be understood that these compositions can also be by other Popular name synonym, by CAS registration number or known by the nomenclature of more elegant, such as IUPAC nomenclature.Additionally, it is skilled Perfumer will be familiar with these synonyms, and the name of more elegant, or at least it is known that Standard reference works, such as The Good Scent Company website, it comprises the custom between the fragrance component of all modes comprising in perfumer's palette The comprehensive inventory of relation between name, registration number and more elegant nomenclature.
In the liquid fragrance composition of the present invention, based on the gross weight of compositionss, the presence of cyclohexylidene phenylacetonitrile Amount can be about 40 to about 95% weight.
In the liquid fragrance composition of the present invention, the amount of component A is liquid fragrance composition about 5 to about 60wt%, and more particularly 10 to 60wt%, are still more particularly 20 to the 60wt% of compositionss, still more particularly It is 25 to the 55wt% for compositionss, and still more particularly 45 to 55wt%.
In the liquid fragrance composition of the present invention, the amount of component B is about the 5 to about 25% of liquid fragrance composition Weight.
The particular liquid flavor compositions of the present invention are by cyclohexylidene phenylacetonitrile (40 to 95 weight %, and more particularly 45 to 55 weight %) and salicylic acid cyclohexyl ester (20 to 60 weight %, and more particularly 45 to 55 weight %) composition.
Another kind of specific liquid fragrance composition of the present invention is by following material composition：
Cyclohexylidene phenylacetonitrile (40 to 95 weight %, and more particularly 45 to 55 weight %)；With salicylic acid cyclohexyl Ester (20 to 60 weight %, and more particularly 45 to 55 weight %)；With
Benzyl alcohol (5 to 25 weight %, and more particularly 10 weight %).
Another kind of specific liquid fragrance composition of the present invention is by following material composition：
Cyclohexylidene phenylacetonitrile (40 to 95 weight %, and more particularly 45 to 55 weight %)；With salicylic acid cyclohexyl Ester (20 to 60 weight %, and more particularly 45 to 55 weight %)；With
The amyl- 1- alcohol of 3- methyl -5- phenyl (5 to 20 weight %, and more particularly 10 weight %).
Mentioned component as the representative component of fluid present invention flavor compositions preferably represents described compositionss Gross mass.However, described liquid fragrance composition may contain the other compositions being usually present in a small amount of impurity or fragrance formulations. Simply by the presence of impurity or other composition, preferably they are not to be exceeded about 0.0001 to about 5 weight % of liquid fragrance composition.
The liquid fragrance composition of the present invention be flowable, dumpable and with storage, transport and use institute The other compositions being usually used in spice under temperature conditionss are had to be blendable.Liquid fragrance composition is being visually inspected When, solid or crystalline material should not contained, and particularly do not contain the cyclohexylidene phenylacetonitrile of solid or crystallization.In the present invention one In individual specific embodiments, liquid fragrance composition is stable, and that is, they are at -20 DEG C to 50 DEG C, more particularly -10 DEG C to 50 DEG C and be not still separated within the temperature range of more particularly -5 DEG C to 50 DEG C.
In one embodiment of the invention, liquid perfume ground compositionss are stable, and that is, they are at -20 DEG C extremely 50 DEG C, more particularly -10 DEG C to 50 DEG C and within the temperature range of still more particularly -5 DEG C to 50 DEG C when storage in a reservoir It is not separated during the time limit of Zhou Zhiyi month.
In one embodiment of the invention, 25 to 250Kg amount liquid fragrance composition be stable, that is, it - 20 DEG C to 50 DEG C, more particularly -10 DEG C to 50 DEG C and within the temperature range of more particularly -5 DEG C to 50 DEG C when being stored in appearance It is not separated during the time limit of a week to month in device.
In one embodiment of the invention, liquid fragrance composition as defined above is stock solution Form.
The stock solution of the present invention is liquid fragrance composition as herein defined, and it is diluted to other fragrance components In to form flavor compositions, itself so can be used for flavouring consumer products.
In a more particular embodiment of the present invention, stock solution is provided containing 25 to 250 liters of stock solutions Container in.
As herein defined liquid fragrance composition is used as the fragrance component in flavor compositions, itself so that can be used for increasing The individual of fragrant form of ownership and household care products.
In addition to liquid fragrance composition, flavor compositions can contain other spice commonly used in the art and become Point, solvent, carrier material and other auxiliary agent.These compositions are described in " perfume and flavor materials of natural or igin”,S.Arctander,Ed.El izabeth,N.J.1960；“Perfume and Flavor Chemicals”,S.Arctander,Ed.Vol I and II,Allured Publishing Corporation,Carol Stream,USA,1994；and“International Cosmetic Ingredient Dictionary”6thEd.,the cosmetic,toiletry and fragrance association,Inc.Washington 1995.
Or, liquid fragrance composition can be used as unique fragrance component in individual or household care products.
Liquid fragrance composition according to the present invention can take the form of the composition in flavor compositions.In this respect, Liquid fragrance composition can be to use cyclohexylidene phenylacetonitrile (Paeonia suffruticosa nitrile with currentTM) the amount that used of makers-up basic Similar amount uses.Especially, the weight based on the flavor compositions comprising it, liquid fragrance composition can with 0.2 to The amount of 20% weight uses.Consumer products include, particularly family and personal care product, including but not limited to solid or liquid Detergent and fabric softener and all common other products in perfumery, i.e. perfume, cologne or shave after shave lotion, Fancy soap, shower or bath salt, mousse, oil or gel, health product or hair care product such as shampoo, body care product, Deodorizer or antiperspirant, air freshener and cosmetic formulations.As detergent, there is expected application, for example, be used for washing Wash or for cleaning composition of detergent or the cleaning product on various surfaces, for example, be used for textile, plate or crust are processed, No matter they are for domestic or industrial use.Other fragranced article include fabric refreshers, press water, paper, cleaning piece or Bleach.
In another aspect of this invention, there is provided to 50 DEG C and still more special to 50 DEG C, more particularly -10 DEG C at -20 DEG C The method that cyclohexylene phenylacetonitrile is in that liquid form is up to time limit one-month period, institute is made at a temperature of not -5 DEG C to 50 DEG C The method of stating includes the step mixing it with component A as defined above and/or component B, to be formed by cyclohexylidene phenyl Acetonitrile and the liquid mixture of component A and/or component B composition.
In order to further illustrate the present invention and its advantage, provide following examples.
Embodiment 1
Cyclohexylidene phenylacetonitrile is mixed with the additive of various amounts to make by using Chemspeed hybrid machine people Standby test sample.Test sample has the size of 25ml, and stores 1 week at 5 DEG C before visual inspection.
The spatula tip keeping the visually sample solid cyclohexylidene phenylacetonitrile for liquid under these conditions connects Kind, and store 1 week at 5 DEG C again.
Finally, kept under these conditions visually be liquid those samples before being visually inspected again warp By -20 DEG C of constant temperature 1 week.
The binary mixture of cyclohexylidene phenylacetonitrile and salicylic acid cyclohexyl ester (50/50wt%) is in all test conditions Under remain liquid.
Cyclohexylidene phenylacetonitrile, salicylic acid cyclohexyl ester also realize similar result with the ternary mixture of benzylalcohol.
The ternary mixture of cyclohexylidene phenylacetonitrile, salicylic acid cyclohexyl ester and the amyl- 1- alcohol of 3- methyl -5- phenyl is also seen Observe similar result.
Cyclohexylidene phenylacetonitrile and PETALIATMMixture crystallization when checking after storing 1 week at 5 DEG C.
It is liquid when the ternary mixture of cyclohexylidene phenylacetonitrile, phenylethyl alcohol and Hexalin checked after 1 week, but After inoculating and storing other one week, its crystallization.Cyclohexylidene phenylacetonitrile and the binary mixture of isopropanol are observed similar Result.

Claims (17)

1. liquid fragrance composition, it is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is one or more of to be selected from the group composition：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- benzene Base-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), phthalic acid two Ethyl ester, isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isoborneol Ester, salicylic acid cis -3- hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester and salicylic acid phenyl Ethyl ester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With optional
Component B, it is one or more of following material：Rose oxideTM, super Herba ConvallariaeTM(6- ethyl -3- methyl -6- octene - 1- alcohol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- trimethyl -2,5- octadiene -4- ketone), new Flos Rosae Rugosae esterTM(2,2- Neopentanoic acid phenylethylester), PEOMOSATM(2- aminomethyl phenyl ethyl alcohol), ROSAPHENTM(2- methyl -5- phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-tetrahydro -2H- pyrans), diphenyl ether, remember promiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- phenyl but-2-ene nitrile, the amyl- 2- alkene of 3- ethyl -2- phenyl Nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise the alcohol more than 3 carbon atoms, selected from benzylalcohol, 1- hexanol, 1-heptanol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol and dimethyl benzyl carbinol；Or glycol ethers.
2. liquid fragrance composition according to claim 1, it is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is one or more of to be selected from the group composition：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- benzene Base-amyl- 1- alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), phthalic acid two Ethyl ester, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, the cis -3- of salicylic acid Hexene base ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester and salicylic acid phenylethylester and KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester).
3. the liquid fragrance composition according to claim 1 or claim 2, it is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the salicylate in being selected from the group：Salicylic acid cyclohexyl ester, salicylic acid isobornyl thiocyanoacetate, and salicylic acid phenyl Ethyl ester.
4. the liquid fragrance composition according to any one of the claims, it is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the composition in being selected from the group：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- phenyl-amyl- 1- Alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), diethyl phthalate, Isopropyl myristate, salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, bigcatkin willow Cis -3- hexene the base ester of acid, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester and salicylic acid phenylethylester With KARMAFLOR (salicylic acid (Z)-hept- 4- alkene -2- base ester)；With
Component B, it is one or more of following material：3- methyl -5- phenyl amyl- 1- alcohol (Flos Rosae Rugosae alcoholTM), rose oxideTM, Super Herba ConvallariaeTM(6- ethyl -3- methyl -6- octen-1-ol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- trimethyl- 2,5- octadiene -4- ketone), new Flos Rosae Rugosae esterTM(PA phenylethylester), PEOMOSATM(2- aminomethyl phenyl ethyl Alcohol), ROSAPHENTM(2- methyl -5- phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-tetrahydro - 2H- pyrans), diphenyl ether, remember promiseTM(1- hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- benzene Base but-2-ene nitrile, 3- ethyl -2- phenyl amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise more than 3 carbon atoms Alcohol, selected from benzylalcohol, 1- hexanol, 1-heptanol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol and Dimethyl benzyl carbinol；Or glycol ethers.
5. the liquid fragrance composition according to any one of the claims, it is substantially by following material composition：
Cyclohexylidene phenylacetonitrile；With
Component A, it is the composition in being selected from the group：Salicylic acid cyclohexyl ester, Flos Rosae Rugosae alcoholTM(3- methyl -5- phenyl-amyl- 1- Alcohol), MDJTM(2- (3- oxo -2- amyl group cyclopenta) acetoxymethyl ester), diethyl phthalate, Salicylic acid amyl group ester, salicylic acid isoamyl base ester, salicylic acid benzyl ester, salicylic acid isobornyl thiocyanoacetate, salicylic acid cis -3- hexenyl Ester, salicylic acid ethyl ester, salicylic acid isobutyl, salicylic acid ester and salicylic acid phenylethylester and KARMAFLOR (bigcatkin willow Sour (Z)-hept- 4- alkene -2- base ester)；With
Component B, it is amyl- 1- alcohol (the Flos Rosae Rugosae alcohol of 3- methyl -5- phenylTM) rose oxideTM, super Herba ConvallariaeTM(6- ethyl -3- first Base -6- octen-1-ol), dimethyl benzyl carbinol, POMAROSETM(5,6,7- trimethyl -2,5- octadiene -4- ketone), new Flos Rosae Rugosae EsterTM(PA phenylethylester), PEOMOSATM(2- aminomethyl phenyl ethyl alcohol), ROSAPHENTM(2- methyl -5- Phenyl-amyl- 1- alcohol), Herba Pelargonii Graveolentiss pyransTM(2- methyl -4- methylene -6- phenyl-tetrahydro -2H- pyrans), diphenyl ether, remember promiseTM(1- Hydroxyl -2- (1- methyl isophthalic acid-hydroxyethyl) -5- hexahydrotoluene), 3- methyl -2- phenyl but-2-ene nitrile, 3- ethyl -2- phenyl Amyl- 2- alkene nitrile or (Z) -2- phenyl hex- 2- alkene nitrile；Comprise the alcohol more than 3 carbon atoms, selected from benzylalcohol, 1- hexanol, 1-heptanol, 1- capryl alcohol, Hexalin, cyclohexyl propanol, methyl phenyl carbinol, phenylethyl alcohol；And dimethyl benzyl carbinol；Or glycol ethers.
6. the liquid fragrance composition according to any one of the claims, wherein said glycol ethers are selected from：Propylene glycol, a contracting two Propylene glycol, 1- methoxy-2-propanol DOWANOLTMPM or 2- (2- methoxy propoxy) propyl- 1- alcohol DOWANOLTMDPM.
7. the liquid fragrance composition according to any one of the claims, substantially by following material composition：Cyclohexylidene benzene Base acetonitrile；Salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid phenylethylester；With optional Amyl- 1- alcohol (the Flos Rosae Rugosae alcohol of 3- methyl -5- phenylTM).
8. the liquid fragrance composition according to any one of claim 1-6, it is substantially by following material composition：Cyclohexylidene benzene Base acetonitrile；Salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid phenylethylester；With optional Benzyl alcohol or 1- hexanol, 1-heptanol or 1- capryl alcohol or Hexalin or cyclohexyl propanol or methyl phenyl carbinol or phenylethyl alcohol Or dimethyl benzyl carbinol.
9. the liquid fragrance composition according to any one of claim 1-6, it is substantially by following material composition：Cyclohexylidene benzene Base acetonitrile；Salicylic acid cyclohexyl ester or salicylic acid benzyl ester or salicylic acid isobornyl thiocyanoacetate or salicylic acid phenylethylester；With optional Glycol ethers, more particularly still, wherein said glycol ethers are propylene glycol or dipropylene glycol or 1- methoxy-2-propanol DOWANOLTMPM or 2- (2- methoxy propoxy) propyl- 1- alcohol DOWANOLTMDPM.
10. the liquid fragrance composition according to any one of the claims, the content of wherein said cyclohexylidene phenylacetonitrile About 40 to about 95% weight for described liquid fragrance composition.
11. are combined with described liquid perfume according to the liquid fragrance composition of any one of the claims, wherein said component A About the 5 of thing exist to about 60wt%.
12. are combined with described liquid perfume according to the liquid fragrance composition of any one of the claims, wherein said component B About the 5 of thing exist to about 25% weight.
13. according to the liquid fragrance composition of any one of the claims, and it is by cyclohexylidene phenylacetonitrile (about 40 to about 95 Weight %) and salicylic acid cyclohexyl ester (about 20 to about 60 weight %) composition.
14. according to the liquid fragrance composition of any one of the claims, and, at -20 DEG C to 50 DEG C, more particularly -10 DEG C extremely for it 50 DEG C, and still more particularly -5 DEG C to 50 DEG C of temperature range was not separated in one week to the time limit of month.
15. according to the liquid fragrance composition of any one of the claims, and it is the form of stock solution.
The purposes of liquid fragrance composition defined in 16. aforementioned any one of claim, it is personal as fragrance component flavouring And household care products.
17. make the side that cyclohexylene phenylacetonitrile is in that liquid form is up to time limit one-month period at a temperature of -20 DEG C to 50 DEG C Method, is mixed to form liquid mixture with component A and optional component B defined in aforementioned any one of claim including by it Step, described liquid mixture is made up of cyclohexylidene phenylacetonitrile and component A and optional component B.
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